It is known that certain alkali metal hydroxides, amines, tertiary phosphines and quaternary ammonium hydroxide resins will catalyze the reaction between a monohydroxy compound and a vicinal epoxide to produce either a monomeric ether of the corresponding monoglycol or a monoether of a polyalkylene glycol. When soluble catalyst such as certain alkali metal hydroxides, low molecular weight amines or tertiary phosphines are used, the catalyst is removed from the reaction mixture with difficulty. When a polymeric, insoluble, quaternary ammonium hydroxide is the catalyst, it deteriorates readily at the reaction temperatures used and, thus, must either be replenished during the reaction, or the reaction may have to be terminated before completion. The quaternary ammonium hydroxide containing polymers cannot be reused for catalytic purposes.
It is, therefore, an object of this invention to provide a catalytic process for reacting an organic monohydroxy compound (alcohol or phenol) with a 1,2 or 1,3 epoxide to produce a monomeric ether of a glycol, or a polyalkylene glycol in which process the catalyst is reusable and easily separated from the reaction mixture.